Asymmetric Synthesis of α,β-Dialkyl-α-phenylalanines via Direct Alkylation of a Chiral Alanine Derivative with Racemic α-Alkylbenzyl Bromides. A Case of High Enantiomer Differentiation at Room Temperature

(Matrix Presented) This study demonstrates that the direct alkylation of a Ni(ll)-complex of the chiral Schiff base of alanine with (S)-o-[N-(N-benzylprolyl)amino]-benzophenone, with racemic α-alkylbenzyl bromides, is a synthetically feasible and methodologically advantageous approach to the target α,β-dialkylphenylalanines over previously reported methods. For the first time we report and rationalize a case of a high enantiomer differentiation process at room temperature.